Palladium-Catalyzed C3-Carbaldehyde Directed Regioselective C2-Thioarylation of Indoles
Sandip Kumar Gupta1, Niranjan Panda1
1Department of Chemistry, National Institute of Technology, Rourkela, Odisha, 769008, India.
Abstract:
Palladium-catalyzed thioarylation of indoles by diaryl disulfides in the presence of phenyliododiacetate is reported. The directing potential of weakly coordinating aldehyde group present at 3-position of indole was exploited for regioselective C2-H thioarylation over the possible C4-H functionalization. Mechanistic studies reveal that the process involves initial generation of thioaryl radical followed by sequential C-H activation, thiolate transfer, and reductive elimination.
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